N,N,2-trimethylaniline

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:120.01; pressure:0.00; stir:

Procedure: Prepared from N,N,2-trimethylaniline (1d, 13.5 mg, 0.100 mmol, 1.00 equiv) and catBH (60.0 mg, 0.500 mmol, 5.00 equiv) under neat conditions according to GP 1. The title compound was purified by flash column chromatography using cyclohexane/EtOAc/Et3N (30/1/1) as eluent to afford 3d (14.3 mg, 55%) as a colorless liquid.

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In the same apparatus and procedure as Example 1 above, 0.06 g (0.45 mmol) of N,N-dimethyltoluidine, 0.7 g (4.5 mmol) of 4-methoxybenzyl chloride, and 3.05 g (22.5 mmol) of trichlorosilane were reacted at 200+ C. for 15 hrs. The resulting mixture was distilled to give 0.13 g of (4-methoxybenzyl)trichlorosilane (yield; 11%). The resulting mixture was distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In the same apparatus and procedure as Example 1 above, 0.06 g (0.45 mmol) of N,N-dimethyltoluidine, 0.7 g (4.5 mmol) of 4-methoxybenzyl chloride, and 3.05 g (22.5 mmol) of trichlorosilane were reacted at 200+ C. for 15 hrs. The resulting mixture was distilled to give 0.13 g of (4-methoxybenzyl)trichlorosilane (yield; 11%). The resulting mixture was distilled

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared by heating 2-chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid and trimethylaniline in the presence of potassium carbonate and copper in DMF. The desired product was isolated by silica gel column chromatography using 5% methanol in chloroform as solvent to give a tan solid, mp. 130-135° C. The title compound was prepared

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The title compound was prepared by heating 2-chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid and trimethylaniline in the presence of potassium carbonate and copper in DMF. The desired product was isolated by silica gel column chromatography using 5% methanol in chloroform as solvent to give a tan solid, mp. 130-135° C. The title compound was prepared

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 2-chloro-4-(1-ethyl-propylamino)-6-methyl-nicotinic acid methyl ester, trimethylaniline, potassium carbonate, copper in DMF was heated at reflux. The mixture was quenched with ammonium chloride and stirred for 20 min, filtered through celite and washed with ethyl acetate. The filtrate was extracted with ethyl acetate. The organic layer was separated, dried and concentrated to dryness. The residue was purified through silica gel column chromatography using 2% methanol in chloroform as eluent to give the title compound as a solid. was heated at reflux The mixture was quenched with ammonium chloride filtered through celite washed with ethyl acetate The filtrate was extracted with ethyl acetate The organic layer was separated dried concentrated to dryness The residue was purified through silica gel column chromatography